132682-35-0Relevant academic research and scientific papers
Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion
Zhou, Zijun,Tan, Yuqi,Shen, Xiang,Ivlev, Sergei,Meggers, Eric
, p. 452 - 458 (2020/12/31)
Chiral β-amino alcohols are important building blocks for the synthesis of drugs, natural products, chiral auxiliaries, chiral ligands and chiral organocatalysts. The catalytic asymmetric β-amination of alcohols offers a direct strategy to access this class of molecules. Herein, we report a general intramolecular C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral β-amino alcohols. Specifically, the ring-closing C(sp3)-H amination of N-benzoyloxycarbamates with 2 mol% of a chiral ruthenium catalyst provides cyclic carbamates in up to 99% yield and with up to 99% ee. The method is applicable to benzylic, allylic, and propargylic C-H bonds and can even be applied to completely non-activated C (sp3)-H bonds, although with somewhat reduced yields and stereoselectivities. The obtained cyclic carbamates can subsequently be hydrolyzed to obtain chiral β-amino alcohols. The method is very practical as the catalyst can be easily synthesized on a gram scale and can be recycled after the reaction for further use. The synthetic value of the new method is demonstrated with the asymmetric synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral β-amino alcohols that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A.[Figure not available: see fulltext.].
Investigations of a nucleophilic alaninol synthon derived from serine
Sibi, Mukund P.,Rutherford, Drew,Renhowe, Paul A.,Li, Biqin
, p. 7509 - 7516 (2007/10/03)
A nucleophilic synthon, (S)-(+)-4-(2-oxazolidonyl)-methyltriphenylphosphinyl iodide 6, available from L-serine in five steps (overall yield of 52%), reacts with aldehydes to produce alkenes in good to excellent yields (74-89%) and, in some cases, provides
A NEW NUCLEOPHILIC ALANINOL SYNTHON FROM SERINE
Sibi, Mukund P.,Renhowe, Paul A.
, p. 7407 - 7410 (2007/10/02)
A new nucleophilic alaninol synthon derived from serine is reported.The utility of this reagent in the stereoselective synthesis of β,γ-unsaturated amino alcohols is described.
